N-bromobutanimide → 3-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine

HRID 2205200Notes

Reaction equation

HRID 2205200 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH3:11])[N:10]=2)[N:7]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:12][C:8]1[N:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 104420726-Chloro-2-methylimidazo(1,2-b)pyridazine

Product 1

HCID 137121543-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazineYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6-chloro-2-methylimidazo[1,2-b]pyridazine (2.00 g, 11.9 mmol, 1.0 equiv) in chloroform (50 mL) was added N-bromosuccinimide (2.55 g, 14.3 mmol, 1.2 equiv). The reaction was stirred at room temperature for 15 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 2.64 g of the yellow solid, 90%.

Workup

  1. customPurification by column chromatography
  2. wash50% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-640d062234ad42fa8b9b04a620e06e43
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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